CA2475011C - Method for analysis of compounds with amino group and analytical reagent therefor - Google Patents
Method for analysis of compounds with amino group and analytical reagent therefor Download PDFInfo
- Publication number
- CA2475011C CA2475011C CA2475011A CA2475011A CA2475011C CA 2475011 C CA2475011 C CA 2475011C CA 2475011 A CA2475011 A CA 2475011A CA 2475011 A CA2475011 A CA 2475011A CA 2475011 C CA2475011 C CA 2475011C
- Authority
- CA
- Canada
- Prior art keywords
- group
- compound
- carbamate
- reagent
- amino group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 125000003277 amino group Chemical group 0.000 title claims abstract description 99
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- 238000004949 mass spectrometry Methods 0.000 claims abstract description 29
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
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Classifications
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
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- G—PHYSICS
- G01—MEASURING; TESTING
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
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- G—PHYSICS
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6806—Determination of free amino acids
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- G—PHYSICS
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6848—Methods of protein analysis involving mass spectrometry
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- G—PHYSICS
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- G01N2458/00—Labels used in chemical analysis of biological material
- G01N2458/15—Non-radioactive isotope labels, e.g. for detection by mass spectrometry
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2560/00—Chemical aspects of mass spectrometric analysis of biological material
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/13—Tracers or tags
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/145555—Hetero-N
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/24—Nuclear magnetic resonance, electron spin resonance or other spin effects or mass spectrometry
Landscapes
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- Health & Medical Sciences (AREA)
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- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
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| JP2002-36446 | 2002-02-14 | ||
| JP2002036446 | 2002-02-14 | ||
| PCT/JP2003/001463 WO2003069328A1 (en) | 2002-02-14 | 2003-02-13 | Method of analyzing aminofunctional compound and analytical reagent |
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| CA2475011C true CA2475011C (en) | 2015-07-07 |
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| EP (3) | EP2336763A1 (enExample) |
| JP (6) | JP4453363B2 (enExample) |
| AU (1) | AU2003211941A1 (enExample) |
| CA (1) | CA2475011C (enExample) |
| WO (1) | WO2003069328A1 (enExample) |
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| EP2336763A1 (en) * | 2002-02-14 | 2011-06-22 | Ajinomoto Co., Inc. | Method for analysis of compounds with amino group and analytical reagent thereof |
| US20050014279A1 (en) * | 2003-07-14 | 2005-01-20 | Nguyen Hoa Duc | Method of analysis of amine by mass spectrometry |
| EP1686372A4 (en) * | 2003-11-21 | 2009-04-01 | Eisai R&D Man Co Ltd | QUANTIFICATION METHOD USING AN ISOTOPE-MARKED INTERNAL CALIBRATION, ANALYSIS SYSTEM FOR EXECUTING THE QUANTIFICATION METHOD AND ASSOCIATED SEPARATION PROGRAM |
| US20070054345A1 (en) | 2004-05-19 | 2007-03-08 | Hunter Christie L | Expression quantification using mass spectrometry |
| US20080206737A1 (en) * | 2004-05-19 | 2008-08-28 | Hunter Christie L | Expression quantification using mass spectrometry |
| WO2005116629A1 (ja) * | 2004-05-26 | 2005-12-08 | Ajinomoto Co., Inc. | アミノ官能性化合物の分析方法及び装置 |
| US20070048752A1 (en) | 2004-07-12 | 2007-03-01 | Applera Corporation | Mass tags for quantitative analyses |
| US20060172319A1 (en) * | 2004-07-12 | 2006-08-03 | Applera Corporation | Mass tags for quantitative analyses |
| US8969089B2 (en) | 2004-10-12 | 2015-03-03 | Quest Diagnostics Investments, Inc. | Analysis of amino acids in body fluid by liquid chromatography-mass spectrometry |
| US20060183238A1 (en) | 2005-02-09 | 2006-08-17 | Applera Corporation | Amine-containing compound analysis methods |
| JP2007163423A (ja) * | 2005-12-16 | 2007-06-28 | Ajinomoto Co Inc | 質量分析計によるアミノ酸分析方法 |
| CN101379074A (zh) * | 2006-02-08 | 2009-03-04 | 日本电气株式会社 | 修饰肽的方法和鉴定肽的方法 |
| WO2007091627A1 (ja) * | 2006-02-08 | 2007-08-16 | Nec Corporation | ペプチドのｃ末端のペプチド結合を切断する方法、及びペプチドのｃ末端アミノ酸配列の決定方法 |
| EP3067692B1 (en) * | 2007-06-29 | 2019-04-17 | Quest Diagnostics Investments Incorporated | Analysis of amino acids in body fluid by liquid chromatography-mass spectrometry (lc-ms) |
| US12367163B2 (en) | 2007-06-29 | 2025-07-22 | Quest Diagnostics Investments Llc | Analysis of amino acids in body fluid by liquid chromatography—mass spectrometry |
| EP2209001A4 (en) | 2007-10-25 | 2010-10-27 | Ajinomoto Kk | METHOD FOR ASSESSING STROKEN GLUCOSE TOLERANCE |
| WO2009070233A1 (en) * | 2007-11-26 | 2009-06-04 | Waters Technologies Corporation | Internal standards and methods for use in quantitatively measuring analytes in a sample |
| DK2252584T3 (en) | 2008-02-04 | 2017-01-16 | Prozyme Inc | COMPOUNDS AND PROCEDURES FOR QUICK LABELING OF N-GLYCANS |
| DE102009060102A1 (de) * | 2009-12-21 | 2011-06-22 | Martin-Luther-Universität Halle-Wittenberg, 06108 | Derivatisierungsreagenzien zur tandem-massenspektrometrischen Quantifizierung von Proteinen |
| KR102002770B1 (ko) | 2011-07-21 | 2019-07-24 | 후지필름 와코 준야꾸 가부시키가이샤 | 혈장중 아미노산 분석용 표준액 |
| US10416166B2 (en) | 2011-09-28 | 2019-09-17 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| US11352325B2 (en) | 2011-09-28 | 2022-06-07 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| US10436790B2 (en) | 2011-09-28 | 2019-10-08 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| US8916680B2 (en) | 2011-11-23 | 2014-12-23 | Quest Diagnostics Investments, Inc. | Kisspeptin-54 detection by tandem mass spectrometry |
| JP6269502B2 (ja) | 2012-11-27 | 2018-01-31 | 味の素株式会社 | 膵臓癌の評価方法、膵臓癌評価装置、膵臓癌評価方法、膵臓癌評価プログラム、膵臓癌評価システムおよび端末装置 |
| EP3748340B1 (en) | 2014-10-30 | 2022-04-06 | Waters Technologies Corporation | Methods for the rapid preparation of labeled glycosylamines and for the analysis of glycosylated biomolecules producing the same |
| CN111796039B (zh) | 2014-11-13 | 2023-03-17 | 沃特世科技公司 | 快速标记的n-聚糖的液相色谱校准方法 |
| KR101627841B1 (ko) | 2015-05-27 | 2016-06-07 | 다이아텍코리아 주식회사 | 싸이오크로멘 타입 화합물 및 그 용도 |
| HUE059723T2 (hu) | 2015-05-29 | 2022-12-28 | Agilent Technologies Inc | Amintartalmú vegyületek jelölésére szolgáló vegyületek és felhasználásuk |
| CN105548432A (zh) * | 2015-12-18 | 2016-05-04 | 乐普药业股份有限公司 | 一种比伐卢定中氨基酸的检测分析方法 |
| WO2017189357A2 (en) | 2016-04-24 | 2017-11-02 | Waters Technologies Corporation | Charged surface reversed phase chromatographic materials method for analysis of glycans modified with amphipathic, strongly basic moieties |
| CN109642906A (zh) | 2016-06-21 | 2019-04-16 | 沃特世科技公司 | 对用两亲强碱性部分改性的聚糖进行电喷雾电离的方法 |
| US11061023B2 (en) | 2016-06-21 | 2021-07-13 | Waters Technologies Corporation | Fluorescence tagging of glycans and other biomolecules through reductive amination for enhanced MS signals |
| PL3480599T3 (pl) | 2016-06-30 | 2025-01-13 | Ajinomoto Co., Inc. | Sposób oceniania ketozy poporodowej |
| CN109690297A (zh) | 2016-07-01 | 2019-04-26 | 沃特世科技公司 | 使用分子量截留过滤和过滤器上去糖基化从复杂基质快速制备标记的葡基胺的方法 |
| EP3519832B1 (en) | 2016-10-03 | 2024-04-03 | Waters Technologies Corporation | Labeled glycan amino acid complexes useful in lc-ms analysis and methods of making the same |
| EP3692372B1 (en) * | 2017-09-08 | 2024-04-17 | F. Hoffmann-La Roche AG | Sulfoxide-based reagent for mass spectrometry |
| JP7151723B2 (ja) | 2017-12-28 | 2022-10-12 | 味の素株式会社 | 給餌管理システムおよび給餌管理方法 |
| WO2020067386A1 (ja) | 2018-09-26 | 2020-04-02 | 味の素株式会社 | 軽度認知障害の評価方法、算出方法、評価装置、算出装置、評価プログラム、算出プログラム、記録媒体、評価システムおよび端末装置 |
| CN116773710A (zh) * | 2021-07-13 | 2023-09-19 | 清华大学 | 一种覆盖多种代谢物的代谢组和代谢流的试剂盒和使用方法 |
| CN114354801B (zh) * | 2021-12-31 | 2023-07-18 | 山东大学 | （R）-3-Boc-氨基哌啶中三种氨基吡啶异构体含量的分析方法 |
| CN115925614B (zh) * | 2022-12-02 | 2024-03-08 | 中山大学 | 用于发现可与醛基反应的活性物质的小分子探针 |
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| AU687109B2 (en) * | 1994-07-08 | 1998-02-19 | City Of Hope | N-terminal protein sequencing reagents and methods which form amino acid derivatives |
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| TW358097B (en) * | 1996-05-24 | 1999-05-11 | Hoffmann La Roche | Beta-lactams and their process and pharmaceutical compositions |
| JP4085443B2 (ja) | 1997-05-07 | 2008-05-14 | 株式会社島津製作所 | アミノ酸の分析試薬及びアミノ酸の分析方法 |
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| JP4505905B2 (ja) | 1999-11-22 | 2010-07-21 | 住友化学株式会社 | ペプチドのアミノ酸配列決定方法 |
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| AUPQ664300A0 (en) * | 2000-04-03 | 2000-05-04 | Proteome Systems Ltd | Macromolecule detection |
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| US20060141632A1 (en) * | 2000-07-25 | 2006-06-29 | The Procter & Gamble Co. | New methods and kits for sequencing polypeptides |
| JP3508710B2 (ja) * | 2000-09-01 | 2004-03-22 | 株式会社日立製作所 | アミノ酸分析方法および装置 |
| CA2426728A1 (en) * | 2000-10-23 | 2002-06-13 | Genetics Institute, Llc. | Isotope-coded ionization-enhancing reagents (icier) for high-throughput protein identification and quantitation using matrix-assisted laser desorption ionization mass spectrometry |
| JP2004531694A (ja) * | 2000-10-23 | 2004-10-14 | ジェネティックス インスティテュート エルエルシー | 酸不安定同位体コード抽出剤（ａｌｉｃｅ）及びタンパク質混合物の定量的マススペクトロメトリック分析におけるその使用 |
| US20030045552A1 (en) * | 2000-12-27 | 2003-03-06 | Robarge Michael J. | Isoindole-imide compounds, compositions, and uses thereof |
| US6818454B2 (en) * | 2001-02-16 | 2004-11-16 | Battelle Memorial Institute | Phosphoprotein binding agents and methods of their use |
| JP3464665B2 (ja) | 2002-01-07 | 2003-11-10 | 株式会社日立製作所 | アミノ酸分析装置 |
| EP2336763A1 (en) * | 2002-02-14 | 2011-06-22 | Ajinomoto Co., Inc. | Method for analysis of compounds with amino group and analytical reagent thereof |
| WO2005116629A1 (ja) * | 2004-05-26 | 2005-12-08 | Ajinomoto Co., Inc. | アミノ官能性化合物の分析方法及び装置 |
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| EP1475632A1 (en) | 2004-11-10 |
| EP1475632B1 (en) | 2013-05-22 |
| JP5842775B2 (ja) | 2016-01-13 |
| US20160139134A1 (en) | 2016-05-19 |
| JP5136542B2 (ja) | 2013-02-06 |
| JP4453363B2 (ja) | 2010-04-21 |
| US9658234B2 (en) | 2017-05-23 |
| AU2003211941A1 (en) | 2003-09-04 |
| US20060286673A1 (en) | 2006-12-21 |
| JPWO2003069328A1 (ja) | 2005-06-09 |
| WO2003069328A1 (en) | 2003-08-21 |
| JP6278210B2 (ja) | 2018-02-14 |
| EP2336763A1 (en) | 2011-06-22 |
| US9274123B2 (en) | 2016-03-01 |
| US20050079624A1 (en) | 2005-04-14 |
| EP2317307B1 (en) | 2013-11-20 |
| EP1475632A4 (en) | 2008-06-25 |
| JP6699645B2 (ja) | 2020-05-27 |
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